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How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
224 Episodes
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If “fixed income is broken,” what are investors actually missing—and how should they rebuild the 40% to protect and compound through drawdowns?
In this episode, I speak with Thomas E. Swaney II, former Chief Investment Officer of Global Fixed Income at Northern Trust Asset Management, who oversaw more than $600 billion across global fixed income. Thomas explains why traditional bond allocations fail when it matters most, how to separate duration from credit risk, and how to use notional leverage to target true diversification without sacrificing liquidity. We explore the structural flaws in 60/40, how to design a fixed income portfolio that actually offsets equity drawdowns, and why the future of bond investing depends on better risk budgeting—not higher yield.
What are the real playbooks behind managing an $86B alternative asset platform—and where do the next decade’s returns actually come from?
In this episode, I sit down with Payton Brooks, Managing Director on Future Standard’s Primary Investments team, to unpack the operating system behind a multi-strategy LP: how a combined platform serves both institutions and the wealth channel, why mid-market private equity still offers the best shot at alpha, and how evergreen structures can reduce cash drag while preserving optionality. We cover sourcing (spinouts, emerging managers), what great GPs do in downturns, the co-invest / secondaries / credit toolkit, and the partnership behaviors that earn re-ups across multiple fund cycles.
Why do ~90% of first-time managers fail before Fund II/III—and what separates durable fund builders from good investors?
In this episode, I unpack that question with Conrad Shang, Founder & Managing Partner at Ensemble VC. We examine why being a great investor is necessary but not sufficient to be a great fund manager, how to build for durability across cycles, and the partnership practices that earn long-term LP trust. Conrad shares lessons from UTIMCO, Norwest, and Bain Capital Ventures; why sometimes the hardest move is sitting out frothy markets; and how Ensemble uses a team-first lens and internal data products to focus time on the few opportunities that matter. We also discuss defense tech’s shift from “taboo” to mainstream, and why communication cadence and transparency determine who survives the first four to five years—when most managers wash out.
What really happens inside the hidden world of family offices—and why do they invest so differently from institutions?
In this episode, I explore that question with Sid Malhotra, Chief Investment Officer at Kactus Capital, a single family office. Sid reveals how family offices align incentives between principals and investment teams, the advantages of having true “skin in the game,” and why their long-term, absolute-return mindset stands apart from pensions, endowments, and foundations. We also discuss the unique strategic role family offices play—from backing zero-to-one opportunities to leveraging deep sector expertise and networks—and how Sid’s career path, from Citadel to Pritzker Group to his current role, shaped his approach to risk, alignment, and building resilient portfolios.
Why is up to “$150 trillion” poised to migrate from public to private markets—and what will unlock that shift for RIAs and family offices?
In this episode, I examine that question with David Sawyer, CEO & Co-Founder of Unlimited.ai. We unpack the real blockers to alternatives adoption—operational, reporting, diligence, and liquidity complexity—and how AI can turn PDFs and siloed portals into queryable, decision-ready data for LPs. We talk RIA psychology, the GP/LP information asymmetry, and why solving “complexity” is the catalyst for the public-to-private transition cited by industry leaders (including the oft-quoted $150T prediction).
How do you underwrite pre-seed founders when the only durable asset is the human—before there’s product-market fit?
In this episode, I go deep with Mike Ma, Managing Partner at Sidecut Ventures, on his 30-day “work-alongside” diligence, why he optimizes for action-oriented self-awareness, and how to calibrate coachability—especially in go-to-market—without overfitting to investor bias. We unpack earned secrets, impact theses in education, climate, healthcare, and economic mobility, solo-GP advantages, alignment pitfalls from 2021-era rounds, and the mindset habits he wishes he’d had earlier: “write at a fourth-grade level” and “document your screw-ups.”
How can families preserve wealth and well-being across five or more generations?
In this episode, I dive deep into a conversation with James E. “Jay” Hughes, Jr., legendary family wealth advisor and author of five influential books including Family Wealth. Jay shares stories from advising families for over 50 years—why flourishing, not just financial returns, is the real measure of wealth; how families like the Rothschilds and Fords illustrate both triumph and tragedy; and why choosing trustees wisely may be the single most important decision for multi-generational continuity. We explore governance, purpose, philanthropy, Aristotle’s philosophy of flourishing societies, and Jay’s own midlife realization that the true professional question is not “what do you need?” but “how can I help?”
How should a public pension build an active equity and absolute-return program—without diluting alpha or chasing the “hot” manager?
In this episode, I go deep with Brian Miller, Senior Investment Officer at the Sacramento County Employees’ Retirement System (SCERS), on constructing a $6B public-equity book inside a ~$15B plan, sizing managers, and using absolute-return strategies as true diversifiers. Brian reflects on 16 years at Tukman Grossman Capital Management (value, long-term compounding, and staying consistent), the realities of “LP capture” across cycles, and why tracking error isn’t the right risk lens. We unpack manager due diligence (including on-site visits), active vs. passive trade-offs, the global/US mix, and how SCERS uses MSCI Caissa for whole-portfolio visibility.
How can continuation vehicles and independent sponsors unlock structural alpha in private equity when traditional buyouts are struggling with low DPI?
In this episode, I go deep with Paul Cohn, Co-Founder and Managing Partner of Agility Equity Partners, on why continuation vehicles (CVs) and independent sponsor deals are reshaping the buyout landscape. Paul explains how CVs let GPs hold their best companies longer while still providing LP liquidity, why the lower middle market offers outsized return potential, and what makes independent sponsors a fast-growing segment of private equity. We cover alignment dynamics, incentives, real-world deal structures, the findings from the HEC Paris study on CVs, and the lessons Paul has learned over 15+ years investing in this niche.
Can venture capital be reinvented to deliver alpha without relying on “heroic assumptions”?
In this episode, I go deep with Daniel Kimerling, Founder and Managing Partner of Deciens Capital, on his mission to build a different kind of venture fund—one focused on highly concentrated, long-duration bets in financial services. Dan explains why Deciens is unapologetically “get rich or die trying,” how his team avoids the venture hamster wheel of markups and momentum rounds, and why he believes the next generation of financial institutions (not just fintech apps) will be the true power-law winners. We cover his philosophy on portfolio construction, long timelines, liquidity vs. exits, and how Deciens publishes its playbooks openly to challenge orthodoxy.
How can ultra-high-net-worth families invest like endowments—without becoming forced sellers when markets turn?
In this episode, I go deep with Greg Brown, Co-CEO of Caprock, on how a modern multi-family office serves UHNW families. Greg explains why Caprock acts as CFO first and CIO second, forecasting liquidity across complex balance sheets before allocating to private markets. We cover the thresholds for when privates make sense, how to structure portfolios for resilience, the role (and limits) of interval funds, and how Caprock uses pooled scale to negotiate economics and secure access to top deals. We also explore tax-alpha strategies like QSBS, Opportunity Zones, and long/short overlays.
How do you run a $1B endowment with a lean five-person team — while balancing liquidity, access, and high-conviction relationships?
In this episode, I speak with Geeta Kapadia, CFA, Chief Investment Officer at Fordham University, about how she manages a concentrated portfolio of 30–40 manager relationships, the lessons she’s learned resetting the portfolio for liquidity, and why she favors passive equities with selective active bets in emerging markets and developed ex-US. We also dive into the shortcomings of interval funds, when to say yes to continuation vehicles, and how Fordham leverages the Gabelli alumni network and a student venture fund to extend sourcing and diligence reach.
How do you use the SBIC program to access long-dated, low-cost leverage—without blowing up risk?
In this episode, I speak with Eric Rosiak, CEO & CIO of Amplify Community Investment Partners, about the mechanics of SBICs, the new accrual debenture license for venture and growth, what top LPs look for, and how policy changes could expand the opportunity set. We dig into eligibility tests, realistic fund sizes, diligence standards (they’re no joke), and why some large platforms now run SBIC sleeves alongside billion-dollar flagships.
What would the bond market look like if it were built today?
In this episode, I speak with Dylan Parker, CEO & Co-Founder of Moment, the operating system for fixed income that unifies trading, portfolio construction, and risk/compliance—and automates the workflows wealth platforms run every day. We dig into how fixed income finally went electronic, why half of bond trading still happens by phone or chat, and how Moment can build customized ladders in seconds instead of hours. We also unpack the (surprisingly big) after-tax edge in munis, and Dylan’s lessons from building automated credit trading at Citadel before raising a $36M Series B led by Index Ventures this summer.
What does it take to build an AI-native search engine for science?
In this episode, I spoke with Eric Olson, Co-founder & CEO of Consensus, the platform making peer-reviewed research accessible through AI. We covered the company’s journey from Series A to millions of users, the realities of competing with tech giants, and what truly creates defensibility for AI startups. Eric shared his perspective on the “AI talent wars,” building products at hyperspeed, and what truly creates a moat for AI applications. If you allocate to or invest in AI, you’ll want to hear Eric’s frameworks for product strategy, market sizing, and execution speed.
In this episode, I speak with Avy Stein, Founder & Chairman of Cresset—a multi-family office known for its private markets access and co-investing model. We cover Avy’s path from Kirkland & Ellis lawyer to private-equity dealmaker, the Willis-Stein spinout from Continental Bank, why multi-strategy platforms scaled so quickly, how co-invest rights really add alpha (and where adverse selection bites), and the rise of private credit in the middle and lower-middle market. We also get into culture building at scale, how Cresset thinks about alignment with GPs, and Avy’s best career advice from four decades in law, PE, operating, and wealth.
In this episode of How I Invest, I speak with Frank Mihail, CIO of the North Dakota Department of Trust Lands, which manages an $8B sovereign wealth endowment built to fund public schools.
Frank shares how his three-person team runs a highly concentrated portfolio with 75% in alternatives, why they prefer evergreen fund structures for liquidity, and how they think about portable alpha, co-investments, and core-satellite strategies.
We also discuss the trust’s broader mission: having already distributed $2B to North Dakota schools, with the long-term goal of covering the entire cost of public education.
What happens when AI lets five people build what used to take fifty? Can you scale to eight figures in revenue without ever touching a “Series A treadmill”? In this episode, I talk with Henry Shi, co-founder of Super.com and creator of the Lean AI Leaderboard, about seedstrapping (raising once, then reaching escape velocity), outcome-based pricing, and a new, non-dilutive way to finance lean, profitable startups. We also get into how Henry “vibe-coded” an AI VC tool over a weekend, why survival rates should improve in the lean-AI era, and what founder traits show up again and again among these ultra-efficient companies.
I had the chance to talk with Francis X. Suarez, the 43rd Mayor of Miami, about how his "open-for-business" leadership transformed the city into a global tech and finance hub. We unpack Miami’s “quantum opportunity,” the practical growing pains—housing, schools, transit—and the civic strategy behind international diplomacy and major sports deals. We also explore his run as President of the U.S. Conference of Mayors and his reflections on leadership, resilience, and embracing failure.
Alan Zafran, Founder & Managing Partner at IEQ Capital, joins to unpack how ultra-high-net-worth families and institutions think about risk, cash runways, GP selection, illiquidity, secondaries, LPAC governance, and portfolio strategy amid rising rates and sovereign debt.
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